How Twitter's CEO 'Screwed Up in Many, Many, Many Ways'

Somewhere on the way to the ultimate Silicon Valley jackpot, Evan Williams lost his grip on Twitter, the microblogging startup he co-founded. He's now out as CEO. What went wrong? So many things.

The New York Times published a lengthy story about Williams at turns friendly to the serial web entrepreneur and lacerating in its examination of his past. Writer Claire Cain Miller leaves you with the impression Williams, who also co-founded Blogger.com and sold it to Google, should never have been running Twitter in the first place. Williams was replaced by COO Dick Costolo in October; the company spun the move as Williams' decision, but insiders had been whispering for months about how Twitter's board was unhappy with him.

Williams is surprisingly open about his leadership failings in the Times piece. At one point he told Miller, "I've been studying this stuff for a really long time, and I've screwed up in many, many, many ways in terms of managing people and product decisions and business."

What are these "many, many, many" screw ups? Williams says he learned a lot from them, which means others can, too. From the article:

Acting like a usurping Johnny Come Lately: When Twitter began, Williams was not involved day to day. He was busy running his startup incubator Obvious Corp. and content as chairman, letting Jack Dorsey, who had come up with the idea of Twitter, run the outfit. But then the microblogging company took off, and Williams joined full time.

When Mr. Williams decided to join Twitter full time in the spring of 2008, his relationship with Mr. Dorsey quickly became strained as the two men competed for power.By the end of 2008, Twitter's growth was exploding - and things inside the company were beginning to break down. Mr. Williams suggested to Twitter's board that it push Mr. Dorsey out.

"There was a feeling that Ev wanted to take control after he realized the potential importance of Twitter," says a Twitter employee who was there during the transition and requested anonymity to protect business relationships.

...Mr. Dorsey declined to comment for this article, but people close to him say he felt betrayed by Mr. Williams.

Dillydallying at a fast-growing company: Twitter's user base exploded in 2008 and 2009, but the company couldn't keep up. The website kept going down and the company was remarkably slow to come up with ways to make money.

What the company needed was simple: people to do all the work. Yet it moved painfully slowly in hiring, with just 110 employees by the end of 2009, even though it had raised $150 million in venture capital by then.

... "Ev is very difficult to work with because he has a tough time making a final decision on products," says the C.E.O. of a Silicon Valley social networking company who requested anonymity because the company works with Twitter. "This all changed when Dick [Costolo] took over. He's very logical and knows how to make things happen."
...

"Dick is hard-charging and very focused on urgency and executing now, and I tend to be very contemplative," [Williams] says. "My weakness is probably taking too long to make a decision, and his is being too hasty."

Alienating employees: Some of Williams' former Blogger employees felt like they got cheated out of their proceeds from the company's sale to Google. Blogger colleague Meg Hourihan is especially blunt:

"I don't think he took care of the people who got him to where he was," says Ms. Hourihan, who earned millions of dollars from the sale. "It was bitter, horrible and tough. He's not C.E.O. material. It doesn't play to his strengths. He's a better inventor; he's better at coming up with ideas."

...Several people who once worked at the company said they didn't make money on the sale because Mr. Williams had never submitted the paperwork needed to allocate stock options. Mr. Williams says that this group hadn't worked at the company long enough for their stock options to vest.

At Twitter, Miller writes that employees were "shocked" when Williams took control from Dorsey, and that Williams can be distant — so quiet in a crowd that "staff members give him a drink and an espresso to loosen him up before big public appearances."